Teal Redmann

Rory's first day at Chilton Prep begins badly when Lorelai accompanies her daughter into the intimidating school wearing a T-shirt, cut-off jeans and cowboy boots, an outfit that draws disapproving stares from the other mothers.

Rory kisses Tristin at a party after fighting with Dean, and Lorelai impulsively shows up at Max's house for a night of lovemaking.

Jess treks to California to stay with his father, and Rory finds out she is ineligible for financial aid.

Still struggling to catch up at Chilton, Rory receives the first `D' of her life on an English assignment and is so humiliated that she plunges into obsessive studying.

Emily throws Rory an elegant birthday party and invites Chilton students, but Rory is embarrassed that the kids she doesn't get along with have been forced to come to the party by their own wealthy parents.

Rory's great-grandmother offers Lorelai a trust fund for Rory's education, causing Emily to fear losing her newfound relationship with them.